Dating a Friend’s Ex: Is It Ever Cool?

I’ve got the biggest thing for my friend’s ex. She’s cute and awesome, and I always thought we would be good together. I really want to give it a shot without causing drama. Is there an easy way to date a friend’s ex, you know, without screwing my friend over?

-Fort Wayne, IN

For this reason alone, I’m glad my friends only date boneheads. Since your friend has better taste, I’ve compiled 3 tips to help you preserve your friendship and get the girl.

TIP #1 Be Honest.

To avoid damaging your friendship, give your friend a heads up. “Mention your desire to date your friend’s ex in a private setting when your friend is in good spirits,” says dating expert, Stephany Alexander. “If you don’t tell your friend, you’re risking your friendship because he might feel like you are going out with his ex behind his back.” Since your friend will inevitably find out, you have nothing to lose–and everything to gain–by addressing your feelings early on.
Ways to start the conversation:Friends come first approach: “I understand things are over between you and your ex. I would like to ask her out to see where it goes. But first, I want to make sure that’s okay with you.”

Nonchalant approach: “I always thought your ex was awesome. Do you care if I give her a call?”

Dude, get over it approach: “It’s been a while since you and the ex went out. It’s cool if I call her, right?”

TIP #2 Consider Timing.

“Some people get over a relationship quickly; others grieve for a lifetime,” says Psychology Today’s Jeremy Nicholson. “But if the friend initiated the break-up or if your friend has moved on to a more satisfying relationship, then it’s probably okay to date the ex.” Stephany Alexander determines the right time differently: “You can use the amount of time they went out to determine how long you should wait. If they dated for only a few months, you could consider mentioning your interest in the ex after 3-6 months.” Regardless of when you decide to bring it up, it’s important that you have this talk.

If your friend says no or dodges your question, reconsider dating the ex. Pursuing her might not be worthwhile if it costs you a close friend and, potentially, your friend group. “Conflicts between friends can force mutual friends to take sides,” says Dr. Nicholson. “It can fracture several friendships.” What will your social life will look like if it’s too awkward for your friend and his ex to attend the same events?

TIP #3 Censor Yourself.

If you have your friend’s blessing, congratulations. Now, make sure your friend doesn’t regret his decision by keeping the details of your new relationship private. “Keep your relationships separate,” says Dr. Nicholson. “The last thing you would want is your new girlfriend talking about her ex, right?”